1H-1,2,4-Triazole → HCID 24954098, compound

Participants

Reaction Conditions

Reaction Steps

To a mixture of copper(I) iodide (0.022 g, 0.12 mmol), trans-N1,N2-dimethylcyclohexane-1,2-diamine (0.027 g, 0.19 mmol), potassium phosphate (0.420 g, 2.0 mmol), 1H-1,2,4-triazole (0.078 g, 1.1 mmol), and (R)—N-(4-chloro-3-iodobenzyl)-1-phenylethanamine 77 (0.352 g, 0.95 mmol) was added DMF (1 mL). The reaction mixture was degassed by a purge/nitrogen cycle (3×) and heated in a sealed tube to 110° C. After 24 h, the reaction mixture was diluted with EtOAc and the organic phase was washed with saturated NH4Cl/NH4OH (10:1) (1×), brine (1×), dried over MgSO4, filtered, and concentrated in vacuo. Purification by flash column chromatography on silica gel (eluted with 10% to 100% EtOAc in hexanes) gave (1R)—N-(4-chloro-3-(1H-1,2,4-triazol-1-yl)benzyl)-1-phenylethanamine 78 (0.031 g, 10% yield) as a colorless oil. 1H NMR (400 MHz, CDCl3) δ 1.38 (d, J=6.5 Hz, 3H), 3.66 (s, 2H), 3.80 (q, J=6.5 Hz, 1H), 7.24-7.36 (m, 7H), 7.48 (d, J=8.2 Hz, 1H), 7.54 (s, 1H), 8.14 (s, 1H), 8.52 (s, 1H). Mass spectrum: calculated for C17H17ClN4 312.1. found 313.2 (M++1).

Provenance & Evidence